Pyrazoloazoles have been known to be useful as magenta dye forming couplers since they were described as being useful for that purpose in Bailey et al. U.S. Pat. No. 3,725,067 issued Apr. 3, 1973. Known processes for preparing these coupler compounds are described, for example, in the Bailey '067 patent, in U.S. Pat. No. 5,055,586 and in Sato, European Published Application 0 476 659, published Mar. 25, 1992. Processes for preparing specific pyrazoloazole compounds are described in Bailey, J. Chem. Soc. Perk. I 2047-52, (1977); Elnagdi et al., J. Het. Chem, 14, 227-30, (1977); and in Farag et al., J. Het. Chem, 24, 1341-44, (1987).
The known processes for preparing pyrazoloazole magenta dye forming couplers add functionality that defines the desired coupler compound early in the synthesis. This results in a lack of generality of the process and the need to make different intermediates for different end coupler compounds.
Furthermore, the known processes for preparing these magenta dye forming couplers involve the use of sulfur-containing intermediates which present a danger of residual sulfur in the compound. Sulfur is a known contaminant for photographic systems.
It would be desirable to have intermediates that could be used to make a variety of end coupler compounds. It also would be desirable to have such intermediates which can be prepared by synthetic routes which do not involve sulfur containing compounds.
We have found such intermediates, methods of making them and methods of using them to make pyrazoloazole photographic couplers.